Deprotonation of β-cyclodextrin in alkaline solutions

Gaidamauskas, Ernestas; Norkus, Eugenijus; Butkus, Eugenijus; Crans, Debbie C.; Grincienė, Giedrė

doi:10.1016/j.carres.2008.10.025

Cited by 72 publications

(41 citation statements)

References 25 publications

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“…Moreover, it has been demonstrated that cyclodextrins form coordination complex with transition metals at high pH values (>12), in such a way that a covalent bond is formed between metal ions (Fe, Ni or Zn) and deprotonated ReOH group, i.e. ReO À group [43]. Thus, it is believed that the combination of these two effects leads the CDs to act as "nanoreactors", modulating the coprecipitation reactions and preventing therefore the growing of the particles.…”

Section: Rheological Characterization Of Feeni/zn and Feni/zn/bcd Susmentioning

confidence: 99%

Modulation of size and viscosity of Ni/Zn ferrites: Effect of doping with βCD and chemical treatment with HNO3 and NaOH

Corrêa

Abrishamkar

Silva

et al. 2015

Journal of Molecular Structure

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Section: Rheological Characterization Of Feeni/zn and Feni/zn/bcd Susmentioning

confidence: 99%

Modulation of size and viscosity of Ni/Zn ferrites: Effect of doping with βCD and chemical treatment with HNO3 and NaOH

Corrêa

Abrishamkar

Silva

et al. 2015

Journal of Molecular Structure

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“…Heating the reaction mixture (up to 70 8C) under variable basic conditions (5.6 % w/w, 40 % w/w and 50 % w/w) led to the partial substitution of all three hydroxyl groups attached to C-2, C-3 and C-6 atoms of bCD units in bCXCDs as from 1 H-NMR characterisation in dimethylsulfoxide (DMSO); this is discussed later in this paper. As a general rule for the reactivity of bCD hydroxyl groups, the primary hydroxyl groups attached to C-6 atom (Figure 1), are considered the most reactive [18][19][20]. The difference of reactivity of the primary and secondary hydroxyl groups of bCD cannot be assessed by the authors in these earlier studies due to the overlap of the hydroxyl proton signals in the NMR analyses.…”

Section: Synthesis Of Bcxcdsmentioning

confidence: 99%

Nitrated Cross‐linked β‐Cyclodextrin Binders Exhibiting Low Glass Transition Temperatures

Luppi

Cavaye

Dossi

2018

Propellants Explo Pyrotec

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Polymeric binders such as β‐cyclodextrins (βCDs) are used to bind with other constituents of energetic formulations and to prevent accidental ignition. One of the advantages of βCDs is the ability to tune their properties by chemical modification. Here, we synthesised nitrated cross‐linked βCDs (βNCXCDs) to produce new binders for energetic formulations. The cross‐linking of βCD with non‐toxic triethylene glycol diglycidyl ether (TEGDGE, X=T) and poly(ethylene glycol) diglycidyl ethers (PEGDGE, X=P) yielded soft, water soluble oligomeric compounds (βCXCDs) which can improve the processability of energetic formulations and contribute to their desensitisation. When the PEGDGE cross‐linker was used, lower glass transition temperatures were achieved, which extended the operative range of the βCPCD binder to −20 °C. The analogous nitrated systems (βNCXCDs) were therefore synthesised using a 1 : 1 (v/v) ratio of 98 % sulfuric acid/100 % nitric acid or 100 % fuming nitric acid, increasing their solubility in acetone and tetrahydrofuran. The nitrated derivatives were characterised by decomposition temperatures (200 °C) and energies (up to 1750 J g−1) comparable to nitrocellulose. Moreover, the glass transition of the inert βCXCDs at low temperatures (<0 °C) was conserved in the corresponding nitrated βNCXCDs, ensuring the desensitisation of energetic compositions even at low temperatures. This is the first time that nitrated derivatives of βCD with glass transition temperatures below 0 °C have been reported, suggesting such derivatives could make suitable replacements for nitrocellulose and other binders in energetic formulations.

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“…A key parameter in the fabrication of cyclodextrin membranes was the pH of the aqueous phase, which was controlled by addition of sodium hydroxide (NaOH). Hydroxyl groups of β‐CD start to slowly deprotonate above pH 12.0 and do so more rapidly above pH 13.0 . Ionization of OH groups at high pHs avoids aggregation of cyclodextrins, forms the more reactive alkoxide ions, and increases their solubility in water.…”

mentioning

confidence: 99%

Cyclodextrin Films with Fast Solvent Transport and Shape‐Selective Permeability

2017

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This study describes the molecular-level design of a new type of filtration membrane made of crosslinked cyclodextrins-inexpensive macrocycles of glucose, shaped like hollow truncated cones. The channel-like cavities of cyclodextrins spawn numerous paths of defined aperture in the separation layer that can effectively discriminate between molecules. The transport of molecules through these membranes is highly shape-sensitive. In addition, the presence of hydrophobic (cavity) and hydrophilic (ester-crosslinked outer part) domains in these films results in high permeances for both polar and nonpolar solvents.

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Deprotonation of β-cyclodextrin in alkaline solutions

Cited by 72 publications

References 25 publications

Modulation of size and viscosity of Ni/Zn ferrites: Effect of doping with βCD and chemical treatment with HNO3 and NaOH

Modulation of size and viscosity of Ni/Zn ferrites: Effect of doping with βCD and chemical treatment with HNO3 and NaOH

Nitrated Cross‐linked β‐Cyclodextrin Binders Exhibiting Low Glass Transition Temperatures

Cyclodextrin Films with Fast Solvent Transport and Shape‐Selective Permeability

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